Jeffrey Haywood wants to marry to Virginia Embrey. However, Virginia refused to marry unless her older sister, the hard-to-please Angelica gets married first. Angelica, in turn, finds every man she knows too dull and predictable, and for this reason prefers to stay single. Jeff then tries to make Angelica interested in the mild-mannered and timid Reggie Irving passing him off as a notorious playboy to intrigue her. He asks his friend Polly to teach Reggie “how to treat a woman right”, but he turns to be a disastrous learner.

A successful mod photographer in London whose world is bounded by fashion, pop music, marijuana, and easy sex, feels his life is boring and despairing. But in the course of a single day he unknowingly captures a death on film.

Playboy songwriter Brad Allen’s succession of romances annoys his neighbor, interior designer Jan Morrow, who shares a telephone party line with him and hears all his breezy routines.